Novel benzimidazole derivatives, preparation method thereof and use thereof as anti-cancer agent or anti-virus agent comprising the same

Abstract

The present invention provides a benzimidazole derivative represented by the following Chemical Formula 1, a preparation method thereof, and use thereof as an anticancer or anti-virus agent:wherein, R1, R2, R3 and X are as defined in the detailed description and the claims.

What is claimed is: 
     
         1 . A method for preparing a benzimidazole-carbohydrate conjugate compound represented by the following Chemical Formula 1, comprising the steps of: reacting a carbohydrate with a 2-aminobenzimidazole compound of Chemical Formula 1a to form an imine bond: 
       
         
           
           
               
               
           
         
         wherein, 
         in the Chemical Formulas 1 and 1a, 
         R 1  is a residue of a carbohydrate, and the carbohydrate is selected from aldotetrose (e.g., erythrose, threose), aldopentose (e.g., ribose, arabinose, xylose, lixose), aldohexose (e.g., allose, altrose, glucose, mannose, glueOS, idose, galactose, tallose), ketotetrose (e.g., erythrolose), ketopentose (e.g., ribulose, xylulose), ketohexose (eg psicose, fructose, sorbose, tagatose), their isomers, oxides (CHO converts to —COOH), deoxy derivatives (—OH converted to —H, e.g., 2-deoxyribose, 2-deoxyglucose), amino sugar (—OH converted to —NH, e.g., N-acetylglucosamine, N-acetylgalactosamine), glycosides, or disaccharides thereof, preferably, is selected from glucose, fructose, galactose, maltose or xylose; 
         R 2  and R 3  are the same or different and are hydrogen or a substitutable hydrocarbon group, for example, represents an alkyl group having 1 to 10 carbon atoms, an aryl group or a heteroaryl group having 3 to 10 ring atoms, and the alkyl group, the aryl group and the heteroaryl group may be substituted with halogen, cyano, hydroxy, thiol, amino, alkyl, alkyloxy, alkylamino, dialkylamino, aryl, aryloxy, arylamino, diarylamino, aryl or heteroaryl group; and 
         X can be selected from the group consisting of —O—, —S—, —SO—, —SO 2 —, —NH—, —N(R2)-, —CH 2 —, —CH(R 2 )—, and —CO—. 
       
     
     
         2 . The method for preparing a benzimidazole-carbohydrate conjugate compound according to  claim 1 , wherein in the 2-aminobenzimidazole compound of Chemical Formula 1a, a substituent capable of performing an imine reaction is previously protected or blocked. 
     
     
         3 . The method for preparing a benzimidazole-carbohydrate conjugate compound according to  claim 1 , wherein in the 2-aminobenzimidazole compound of Chemical Formula 1a, a substituent capable of performing an imine reaction is previously protected or blocked.